Month: January 2023

Acetylenic derivatives of heterocycles. 8. New route to the synthesis of ethynylpyrazoles was written by Vasilevskii, S. F.;Shvartsberg, M. S.;Kotlyarevskii, I. L.. And the article was included in Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya in 1971.Name: 5-Iodo-1-methyl-1H-pyrazole This article mentions the following:

The catalyzed substitution of halogen by an acetylenic group in heterocyclic compounds was applicable to pyrazoles. BuLi and 1-methylpyrazole mixed in the cold and held 1 hr at room temperature, treated with iodine at 5° and made alk. with aqueous NaOH, gave 5-iodo-1-methylpyrazole, which in AcOH-CCl4 with iodine-HIO3 in the presence of 30% H2SO4 gave in 15 min at 75° the 4,5-diiodo analog. 3,4-Diiodopyrazole and Me2SO4 in dioxane-40% NaOH gave 1-methyl-4,5-diiodopyrazole and the 3,4-diiodo analog in nearly equal yields. Similar methylation was used to prepare 3,4,5-triiodo-1-methylpyrazole. The iodopyrazoles and HCCCMe2OCHMeOEt heated at 111-14° with activated powd. Cu and K2CO3 in pyridine gave the appropriately substituted acetylenic derivatives from stoichiometric proportions of reactants used. These acetals were hydrolyzed with 1:3 aqueous HCl 2-3 hr to the acetylenic alcs. which heated with powd. KOH afforded pyrazolylacetylenes in 41-73% yields. In the experiment, the researchers used many compounds, for example, 5-Iodo-1-methyl-1H-pyrazole (cas: 34091-51-5Name: 5-Iodo-1-methyl-1H-pyrazole).

5-Iodo-1-methyl-1H-pyrazole (cas: 34091-51-5) belongs to iodide derivatives. Organic iodides can be alkyl, alkenyl, or alkynyl, and all of them are very reactive toward with many kinds of nucleophiles. Polyiodoorganic compounds are sometimes employed as X-ray contrast agents, in fluoroscopy, a type of medical imaging. This application exploits the X-ray absorbing ability of the heavy iodine nucleus.Name: 5-Iodo-1-methyl-1H-pyrazole

Referemce:
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

A Simultaneous Reduction, Substitution, and Self-Assembly Reaction under Hydrothermal Conditions Afforded the First Diiodopyridine Copper(I) Coordination Polymer was written by Lu, Jack Y.;Babb, Amy M.. And the article was included in Inorganic Chemistry in 2002.Application In Synthesis of 5-Iodonicotinic acid This article mentions the following:

A simultaneous reduction of Cu(II) to Cu(I) by pyridinecarboxylate and the substitution of carboxylato groups by iodo nucleophiles in a self-assembly process under hydrothermal conditions afforded a new I-inclusion coordination polymer [CuI(C₅H₃NI₂)·¹/₂I₂] 1. The synthetic studies of the substitution process produced a new supramol. compound [IC₅H₃NCOOH] 2 and revealed that the catalytic properties of Cu ions in redox and substitution reactions under hydrothermal conditions are attractive. Crystal data for [CuI(C₅H₃NI₂)·¹/₂I₂]: triclinic, space group P1̅; cell dimensions a 4.216(1), b 11.254(2), c 12.196(2) Å, α 80.34(3), β 88.44(3), γ 83.10(3)°, Z = 2. Crystal data for [IC₅H₃NCOOH]: monoclinic, space group P2₁/c; cell dimensions a 5.041(1), b 17.313(2), c 8.639(1) Å, β 95.042(2)°, Z = 4. In the experiment, the researchers used many compounds, for example, 5-Iodonicotinic acid (cas: 15366-65-1Application In Synthesis of 5-Iodonicotinic acid).

5-Iodonicotinic acid (cas: 15366-65-1) belongs to iodide derivatives. Organic iodides are organic compounds containing a carbon-iodine (C-I) bond. The carbon-iodine bond is weaker than other carbon-halogen bonds due to the poor electronegative nature of the iodine atom. Alkyl iodides react at a faster rate than alkyl fluorides due to the weak C-I bond.Application In Synthesis of 5-Iodonicotinic acid

Referemce:
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Small-Molecule Anticonvulsant Agents with Potent In Vitro Neuroprotection and Favorable Drug-Like Properties was written by Smith, Garry R.;Brenneman, Douglas E.;Zhang, Yan;Du, Yanming;Reitz, Allen B.. And the article was included in Journal of Molecular Neuroscience in 2014.Formula: C6H3F2I This article mentions the following:

Severe seizure activity is associated with reoccurring cycles of excitotoxicity and oxidative stress that result in progressive neuronal damage and death. Intervention with these pathol. processes is a compelling disease-modifying strategy for the treatment of seizure disorders. We have optimized a series of small mols. for neuroprotective and anticonvulsant activity as well as altered their phys. properties to address potential metabolic liabilities, to improve CNS penetration, and to prolong the duration of action in vivo. Utilizing phenotypic screening of hippocampal cultures with nutrient medium depleted of antioxidants as a disease model, cell death and decreased neuronal viability produced by acute treatment with glutamate or hydrogen peroxide were prevented. Modifications to our previously reported proof of concept compounds have resulted in a lead which has full neuroprotective action at <1 nM and antiseizure activity across six animal models including the kindled rat and displays excellent pharmacokinetics including high exposure to the brain. These modifications have also eliminated the requirement for a chiral mol., removing the possibility of racemization and making large-scale synthesis more easily accessible. These studies strengthen our earlier findings which indicate that potent, multifunctional neuroprotective anticonvulsants are feasible within a single mol. entity which also possesses favorable CNS-active drug properties in vitro and in vivo. In the experiment, the researchers used many compounds, for example, 1,2-Difluoro-3-iodobenzene (cas: 64248-57-3Formula: C6H3F2I).

1,2-Difluoro-3-iodobenzene (cas: 64248-57-3) belongs to iodide derivatives. Typical reactions of alkyl iodides include nucleophilic substitution, elimination, reduction, and the formation of organometallics. The C–I bond is the weakest of the carbon–halogen bonds. These bond strengths correlate with the electronegativity of the halogen, decreasing in the order F > Cl > Br > I. This periodic order also follows the atomic radius of halogens and the length of the carbon-halogen bond.Formula: C6H3F2I

Referemce:
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Metal-Free Hypervalent-Iodine-Promoted C3 Difluorination and C2 Oxidation of N-Substituted Indoles was written by Sun, Xin;Zhao, Xiao-Jing;Wu, Bin. And the article was included in Asian Journal of Organic Chemistry in 2017.Computed Properties of C8H7IO4 This article mentions the following:

A metal-free, highly regioselective C3 difluorination and C2 oxidation of N-substituted indoles I (R¹ = 5-Br, 7-Cl, 3,6-F₂, etc.; R² = Bn, 4-ClC₆H₄CH₂, 2,3,5-F₃C₆H₂CH₂, etc.) with the aid of in situ generated PhIF₂ in the presence of two types of fluorinating agents such as Pyr·HF and Et₃N·HF was reported. This reaction provided 3,3-difluoro-2-oxindoles II with yields up to 64% under mild reaction conditions. A mechanism for this reaction was proposed. In the experiment, the researchers used many compounds, for example, Methyl 3,5-dihydroxy-4-iodobenzoate (cas: 338454-02-7Computed Properties of C8H7IO4).

Methyl 3,5-dihydroxy-4-iodobenzoate (cas: 338454-02-7) belongs to iodide derivatives. Organic iodides can be alkyl, alkenyl, or alkynyl, and all of them are very reactive toward with many kinds of nucleophiles. In the chemical industry, alkyl iodides serve as excellent alkylating agents and, specifically, methyl iodide is used as a methylating agent in the synthesis of various pharmaceutical drugs.Computed Properties of C8H7IO4

Referemce:
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Iron(II)-Catalyzed Heck-Type Coupling of Vinylarenes with Alkyl Iodides was written by Xiong, Haigen;Li, Yajun;Qian, Bo;Wei, Rongbiao;Van der Eycken, Erik V.;Bao, Hongli. And the article was included in Organic Letters in 2019.Category: iodides-buliding-blocks This article mentions the following:

An iron(II)-catalyzed radical alkyl Heck-type reaction of alkyl iodides with vinylarenes under mild conditions has been reported. T-Bu peroxybenzoate (TBPB) behaves simultaneously as a radical relay initiator, a precursor for the generation of alkyl radical from alkyl iodides, and an oxidant to recycle iron(II)/iron(III). Unactivated primary, secondary, and tertiary alkyl iodides are compatible with the reaction conditions. The mechanistic studies suggest that a radical-polar-crossover pathway might be involved in the catalytic cycle. In the experiment, the researchers used many compounds, for example, 1-Chloro-4-iodobutane (cas: 10297-05-9Category: iodides-buliding-blocks).

1-Chloro-4-iodobutane (cas: 10297-05-9) belongs to iodide derivatives. Generally organic iodides can be divided into two classes of alkyl iodides and aryl iodides. Typical reactions of alkyl iodides include nucleophilic substitution, elimination, reduction, and the formation of organometallics. In the chemical industry, alkyl iodides serve as excellent alkylating agents and, specifically, methyl iodide is used as a methylating agent in the synthesis of various pharmaceutical drugs.Category: iodides-buliding-blocks

Referemce:
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Synthesis and in vivo brain distribution of carbon-11-labeled δ-opioid receptor agonists was written by Pichika, Rama;Jewett, Douglas M.;Sherman, Philip S.;Traynor, John R.;Husbands, Stephen M.;Woods, James H.;Kilbourn, Michael R.. And the article was included in Nuclear Medicine and Biology in 2010.Application of 77350-52-8 This article mentions the following:

Three new radiolabeled compounds, [¹¹C]SNC80 ((+)-4-[(αR)-α-{(2S,5R)-4-allyl-2,5-dimethyl-1-piperazinyl}]-3-[¹¹C]methoxybenzyl-N,N-diethylbenzamide), N,N-diethyl-4-(3-methoxyphenyl-1-[¹¹C]methylpiperidin-4-ylidenemethyl)benzamide and N,N-diethyl-4-[(1-[¹¹C]methylpiperidin-4-ylidene)phenylmethyl]benzamide, were prepared as potential in vivo radiotracers for the δ-opioid receptor. Each compound was synthesized by alkylation of the appropriate desmethyl compounds using [¹¹C]methyl triflate. In vivo biodistribution studies in mice showed very low initial brain uptake of all three compounds and no regional specific binding for [¹¹C]SNC80. A monkey positron emission tomog. study of [¹¹C]SNC80 confirmed low brain permeability and uniform regional distribution of this class of opioid agonists in a higher species. Opioid receptor ligands of this structural class are thus unlikely to succeed as in vivo radiotracers, likely due to efficient exclusion from the brain by the P-glycoprotein efflux transporter. In the experiment, the researchers used many compounds, for example, N,N-Diethyl-4-iodobenzamide (cas: 77350-52-8Application of 77350-52-8).

N,N-Diethyl-4-iodobenzamide (cas: 77350-52-8) belongs to iodide derivatives. In general, organic iodides are light-sensitive and turn yellow during storage, owing to the formation of iodine. Organoiodine lubricants can be used with titanium, stainless steels, and other metals which tend to seize up with conventional lubricants: organoiodine lubricants can be used in turbines and spacecraft, and as a cutting oil in machining.Application of 77350-52-8

Referemce:
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Efficient iodination of aromatic compounds using potassium ferrate supported on montmorillonite was written by Keipour, Hoda;Khalilzadeh, Mohammad A.;Mohtat, Bita;Hosseini, Abolfazl;Zareyee, Daryoush. And the article was included in Chinese Chemical Letters in 2011.Application In Synthesis of 4,5-Diiodo-1H-imidazole This article mentions the following:

Potassium ferrate impregnated on montmorillonite is a mild, cheap, and non-toxic reagent for the iodination of phenols, including naphthol, aromatic amines, and heterocyclic substrates in fair to excellent yields by a simple isolation procedure. In the experiment, the researchers used many compounds, for example, 4,5-Diiodo-1H-imidazole (cas: 15813-09-9Application In Synthesis of 4,5-Diiodo-1H-imidazole).

4,5-Diiodo-1H-imidazole (cas: 15813-09-9) belongs to iodide derivatives. Organic iodides are organic compounds containing a carbon-iodine (C-I) bond. The carbon-iodine bond is weaker than other carbon-halogen bonds due to the poor electronegative nature of the iodine atom. Alkyl iodides react at a faster rate than alkyl fluorides due to the weak C-I bond.Application In Synthesis of 4,5-Diiodo-1H-imidazole

Referemce:
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Discovery and optimization of a novel CNS penetrant series of mGlu₄ PAMs based on a 1,4-thiazepane core with in vivo efficacy in a preclinical Parkinsonian model was written by Kent, Caitlin N.;Fulton, Mark G.;Stillwell, Kaylee J.;Dickerson, Jonathan W.;Loch, Matthew T.;Rodriguez, Alice L.;Blobaum, Anna L.;Boutaud, Olivier;Rook, Jerri L.;Niswender, Colleen M.;Conn, P. Jeffrey;Lindsley, Craig W.. And the article was included in Bioorganic & Medicinal Chemistry Letters in 2021.Application In Synthesis of 3-Fluoro-5-iodoaniline This article mentions the following:

A high throughput screen (HTS) identified a novel, but weak (EC₅₀ = 6.2μM, 97% Glu Max) mGlu₄ PAM chemotype based on a 1,4-thiazepane core, VU0544412. Reaction development and chem. optimization delivered a potent mGlu₄ PAM VU6022296 (EC₅₀ = 32.8 nM, 108% Glu Max) with good CNS penetration (K_p = 0.45, K_p,uu = 0.70) and enantiopreference. Finally, VU6022296 displayed robust, dose-dependent efficacy in reversing Haloperidol-Induced Catalepsy (HIC), a rodent preclin. Parkinson’s disease model. In the experiment, the researchers used many compounds, for example, 3-Fluoro-5-iodoaniline (cas: 660-49-1Application In Synthesis of 3-Fluoro-5-iodoaniline).

3-Fluoro-5-iodoaniline (cas: 660-49-1) belongs to iodide derivatives. Organic iodides can be alkyl, alkenyl, or alkynyl, and all of them are very reactive toward with many kinds of nucleophiles. A typical method for synthesis of aromatic iodides is diazotization of primary aromatic amines followed by treatment of potassium iodide. Aliphatic alcohols are converted to alkyl iodides by treating with hydrogen iodide.Application In Synthesis of 3-Fluoro-5-iodoaniline

Referemce:
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Total synthesis of keramamides A and L from a common precursor by late-stage indole synthesis and configurational revision was written by Junk, Lukas;Kazmaier, Uli. And the article was included in Angewandte Chemie, International Edition in 2018.SDS of cas: 289039-26-5 This article mentions the following:

The marine natural products keramamide A and L, members of the class of anabaenopeptin-type peptides, were synthesized for the first time by a convergent and flexible route. The installation of the substituted tryptophan moieties was accomplished at the very end of the synthesis on the cyclic peptides, and thus enabled the synthesis of both natural products from one common precursor. The preparation of several epimers clearly indicates that the originally proposed relative configurations of both Keramamides A and L were not correct. In the experiment, the researchers used many compounds, for example, 2-Chloro-5-iodophenol (cas: 289039-26-5SDS of cas: 289039-26-5).

2-Chloro-5-iodophenol (cas: 289039-26-5) belongs to iodide derivatives. Typical reactions of alkyl iodides include nucleophilic substitution, elimination, reduction, and the formation of organometallics. A typical method for synthesis of aromatic iodides is diazotization of primary aromatic amines followed by treatment of potassium iodide. Aliphatic alcohols are converted to alkyl iodides by treating with hydrogen iodide.SDS of cas: 289039-26-5

Referemce:
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Indium-Mediated Synthesis of Heterobiaryls was written by Font-Sanchis, Enrique;Cespedes-Guirao, F. Javier;Sastre-Santos, Angela;Fernandez-Lazaro, Fernando. And the article was included in Journal of Organic Chemistry in 2007.Quality Control of 5-Iodo-1-methyl-1H-pyrazole This article mentions the following:

The palladium-mediated coupling reaction between triorganoindium reagents and heteroaryl iodides is extended to the synthesis of heterobiaryls, e.g., I. Both electron-rich and electron-poor heterocycles can act as the organic electrophile or as the organoindium derivative In the experiment, the researchers used many compounds, for example, 5-Iodo-1-methyl-1H-pyrazole (cas: 34091-51-5Quality Control of 5-Iodo-1-methyl-1H-pyrazole).

5-Iodo-1-methyl-1H-pyrazole (cas: 34091-51-5) belongs to iodide derivatives. Organic iodides are widely used in organic synthesis. Halogenation of aromatic hydrocarbons is a very important reaction via an electrophilic aromatic substitution. Organoiodine lubricants can be used with titanium, stainless steels, and other metals which tend to seize up with conventional lubricants: organoiodine lubricants can be used in turbines and spacecraft, and as a cutting oil in machining.Quality Control of 5-Iodo-1-methyl-1H-pyrazole

Referemce:
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com